Sounds like an awesome way to spend time together and great that your son is enjoying it so much.
About your questions:
2WD vs RWD: 2WD definitely helps with traction, especially on grass, dirt, or hills. It won’t magically “pull over” obstacles like a mound, but it can reduce wheel slip and give better control on uneven terrain. For hill climbing, two motors (even 2×1000W) usually feel stronger and more stable than a single 2500W, mainly because power is distributed to both wheels.
Safety: 2WD isn’t automatically safer, but it gives more grip, which can help in tricky conditions. Still, rider control matters more than drivetrain.
Brakes: What you described with mechanical brakes is pretty common they stretch and need adjustment. If you’re riding regularly, hydraulic brakes are a big upgrade: more consistent, stronger, and less maintenance.
Seated vs standing: For off-road or park riding, standing is generally safer because you can absorb shocks and react faster. Seating is more comfortable, but yeah it can increase risk on uneven ground.
Overall, if you’re planning more off-road and hill riding, 2WD + hydraulic brakes would be a noticeable upgrade.
After rides like that, I usually chill with something simple geometry dash original is a fun way to relax for a bit.